Carbon tetrabromide → HCID 67324904, compound

HRID 1397342Notes

Reaction equation

HRID 1397342 reaction equation
[C:1]([Br:5])(Br)(Br)Br.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:25]1([C:31]2[S:35][C:34](CO)=[N:33][CH:32]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(Cl)Cl>[Br:5][CH2:1][C:34]1[S:35][C:31]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:32][N:33]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 273543HCID 273543, compound

Product 1

HCID 67324904HCID 67324904, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

CBr4 (8.65 g, 26.1 mmol) and Ph3P (5.1 g, 19.6 mmol) were added to a solution of (5-phenylthiazol-2-yl)methanol (2.5 g, 13.07 mmol) in dry CH2Cl2 (30 mL) at 0° C. The resulting reaction mixture was stirred at room temperature for 1 h and then concentrated under reduced pressure. The residue was diluted with diethyl ether and filtered. The clear filtrate was removed under reduced pressure and the crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 5-10% EtOAc in petroleum ether) to afford 2-(bromomethyl)-5-phenylthiazole (2 g, yield 60%). 1H NMR (300 MHz, CDCl3) δ 7.89 (s, 1H), 7.57-7.55 (m, 2H), 7.45-7.36 (m, 3H), 4.76 (s, 2H). MS (ESI) m/z: Calculated for C10H8BrNS: 254.95. found: 256.0 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with diethyl ether
  4. filtrationfiltered
  5. customThe clear filtrate was removed under reduced pressure
  6. customthe crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 5-10% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-9fdbea40b69b4d7a9cc1f051315a168b
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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